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WO2016027401A1 - Procédé de fabrication de polymère de diène conjugué à extrémité modifiée, polymère de diène conjugué à extrémité modifiée, composition de caoutchouc, et pneu - Google Patents

Procédé de fabrication de polymère de diène conjugué à extrémité modifiée, polymère de diène conjugué à extrémité modifiée, composition de caoutchouc, et pneu Download PDF

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Publication number
WO2016027401A1
WO2016027401A1 PCT/JP2015/003347 JP2015003347W WO2016027401A1 WO 2016027401 A1 WO2016027401 A1 WO 2016027401A1 JP 2015003347 W JP2015003347 W JP 2015003347W WO 2016027401 A1 WO2016027401 A1 WO 2016027401A1
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WO
WIPO (PCT)
Prior art keywords
compound
group
atom
conjugated diene
diene polymer
Prior art date
Application number
PCT/JP2015/003347
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English (en)
Japanese (ja)
Inventor
平田　成邦
悠介 山縣
友絵 田邊
会田　昭二郎
Original Assignee
株式会社ブリヂストン
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社ブリヂストン filed Critical 株式会社ブリヂストン
Priority to RU2017108844A priority Critical patent/RU2671351C2/ru
Priority to CN201580044777.0A priority patent/CN106604935B/zh
Priority to US15/503,884 priority patent/US10131722B2/en
Priority to EP15833853.3A priority patent/EP3184554B1/fr
Priority to JP2016543795A priority patent/JP6645969B2/ja
Publication of WO2016027401A1 publication Critical patent/WO2016027401A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/22—Incorporating nitrogen atoms into the molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B60—VEHICLES IN GENERAL
    • B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
    • B60C1/00—Tyres characterised by the chemical composition or the physical arrangement or mixture of the composition
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/25—Incorporating silicon atoms into the molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
    • C08C19/00—Chemical modification of rubber
    • C08C19/30—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule
    • C08C19/42—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups
    • C08C19/44—Addition of a reagent which reacts with a hetero atom or a group containing hetero atoms of the macromolecule reacting with metals or metal-containing groups of polymers containing metal atoms exclusively at one or both ends of the skeleton
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F136/06—Butadiene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F136/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
    • C08F136/02—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
    • C08F136/04—Homopolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
    • C08F136/08—Isoprene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/06—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen
    • C08F4/12—Metallic compounds other than hydrides and other than metallo-organic compounds; Boron halide or aluminium halide complexes with organic compounds containing oxygen of boron, aluminium, gallium, indium, thallium or rare earths
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/54—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with other compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F4/00—Polymerisation catalysts
    • C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
    • C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
    • C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
    • C08F4/602—Component covered by group C08F4/60 with an organo-aluminium compound
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/18—Introducing halogen atoms or halogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/34—Introducing sulfur atoms or sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L15/00—Compositions of rubber derivatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L9/00—Compositions of homopolymers or copolymers of conjugated diene hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2353/00—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
    • C08J2353/02—Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers of vinyl aromatic monomers and conjugated dienes

Definitions

  • the rare earth element compound has the following general formula (a-1): M- (AQ 1 ) (AQ 2 ) (AQ 3 ) (a-1) [Wherein M is a scandium, yttrium or lanthanoid element; AQ 1 , AQ 2 and AQ 3 are functional groups which may be the same or different; A is nitrogen, oxygen or sulfur; Yes; provided that it has at least one MA bond]. This is because the activity of the catalyst can be further increased.
  • examples of the functional group represented by AQ 1 , AQ 2 and AQ 3 include an amide group.
  • the amide group include aliphatic amide groups such as dimethylamide group, diethylamide group and diisopropylamide group; phenylamide group, 2,6-di-tert-butylphenylamide group, 2,6-diisopropylphenylamide group, 2,6-dineobenchylphenylamide group, 2-tert-butyl-6-isopropylphenylamide group, 2-tert-butyl-6-neoventylphenylamide group, 2-isopropyl-6-neobutenylphenyl Amide groups, arylamide groups such as 2,4,6-tert-butylphenylamide groups; bistrialkylsilylamide groups such as bistrimethylsilylamide groups, and in particular, from the viewpoint
  • the aluminoxane represented by (B-2) is a compound obtained by bringing an organoaluminum compound into contact with a condensing agent.
  • R ′ is a hydrocarbon group having 1 to 10 carbon atoms, and some of the hydrocarbon groups may be substituted with a halogen atom and / or an alkoxy group;
  • the polymerization degree of the repeating unit is preferably 5 or more, and more preferably 10 or more.
  • organic compound containing active halogen examples include benzyl chloride.
  • the compounds listed in the compound (f) contain an aprotic polar group such as an ether group or tertiary amino group in the coupling agent molecule as long as the object of the present invention is not impaired. It doesn't matter. Moreover, a compound (f) can be used individually by 1 type, or 2 or more types can also be mixed and used for it. Furthermore, the compound (f) may contain a compound containing a free alcohol group or phenol group as an impurity. Compound (f) may be a single compound or a mixture of two or more of these compounds.
  • Example 9 to 16 Polymer samples were obtained under the same conditions as in Examples 1 to 8, except that 70 g of isoprene was used in place of 70 g of 1,3-butadiene as the conjugated diene compound. The yield of each sample of the polymer obtained was 66 g. The types of modifiers used are shown in Table 2.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerization Catalysts (AREA)

Abstract

La présente invention vise à fournir : un procédé de fabrication d'un polymère de diène conjugué ayant une extrémité modifiée apte à atteindre de très grandes quantités de liaisons cis-1,4 sans nécessiter de conditions de fabrication complexes ; un polymère de diène conjugué ayant une extrémité modifiée obtenu à l'aide dudit procédé de fabrication ; une composition de caoutchouc comprenant ledit polymère de diène conjugué ayant une extrémité modifiée ; et un pneu utilisant ladite composition de caoutchouc. La présente invention concerne un procédé de fabrication d'un polymère de diène conjugué ayant une extrémité modifiée dans lequel un composé de diène conjugué est polymérisé à l'aide d'une composition de catalyseur de polymérisation et le polymère obtenu dans ladite polymérisation est modifié à l'aide d'un agent de modification. Le procédé se caractérise en ce que : ladite composition de catalyseur de polymérisation comprend un composé élément de terres rares ainsi qu'un composé de coordination ayant un squelette cyclopentadiène choisi parmi un cyclopentadiène substitué ou non substitué, un indène substitué ou non substitué, et un fluorène substitué ou non substitué ; et lesdites polymérisation et modification sont réalisées dans un pot unique.
PCT/JP2015/003347 2014-08-20 2015-07-02 Procédé de fabrication de polymère de diène conjugué à extrémité modifiée, polymère de diène conjugué à extrémité modifiée, composition de caoutchouc, et pneu WO2016027401A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
RU2017108844A RU2671351C2 (ru) 2014-08-20 2015-07-02 Способ получения терминально модифицированного полимера сопряженного диена, терминально модифицированный полимер сопряженного диена, резиновая композиция и шина
CN201580044777.0A CN106604935B (zh) 2014-08-20 2015-07-02 末端改性共轭二烯聚合物的制造方法、末端改性共轭二烯聚合物、橡胶组合物、以及轮胎
US15/503,884 US10131722B2 (en) 2014-08-20 2015-07-02 Method for preparing terminal-modified conjugated diene polymer, terminal-modified conjugated diene polymer, rubber composition and tire
EP15833853.3A EP3184554B1 (fr) 2014-08-20 2015-07-02 Procédé de fabrication de polymère de diène conjugué à extrémité modifiée, polymère de diène conjugué à extrémité modifiée, composition de caoutchouc, et pneu
JP2016543795A JP6645969B2 (ja) 2014-08-20 2015-07-02 末端変性共役ジエン重合体の製造方法、末端変性共役ジエン重合体、ゴム組成物及びタイヤ

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2014-167707 2014-08-20
JP2014167707 2014-08-20

Publications (1)

Publication Number Publication Date
WO2016027401A1 true WO2016027401A1 (fr) 2016-02-25

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PCT/JP2015/003347 WO2016027401A1 (fr) 2014-08-20 2015-07-02 Procédé de fabrication de polymère de diène conjugué à extrémité modifiée, polymère de diène conjugué à extrémité modifiée, composition de caoutchouc, et pneu

Country Status (6)

Country Link
US (1) US10131722B2 (fr)
EP (1) EP3184554B1 (fr)
JP (1) JP6645969B2 (fr)
CN (1) CN106604935B (fr)
RU (1) RU2671351C2 (fr)
WO (1) WO2016027401A1 (fr)

Cited By (8)

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JP2017203060A (ja) * 2016-05-09 2017-11-16 株式会社ブリヂストン ゴム組成物およびゴム物品
WO2017195634A1 (fr) * 2016-05-09 2017-11-16 株式会社ブリヂストン Polymère à base de diène conjugué modifié par un élément de terminaison, composition de caoutchouc et article en caoutchouc
WO2017203830A1 (fr) * 2016-05-24 2017-11-30 株式会社ブリヂストン Polymère de diène conjugué à partie terminale modifiée ainsi que procédé de fabrication de celui-ci, composition de caoutchouc, et article en caoutchouc
WO2018151300A1 (fr) * 2017-02-20 2018-08-23 株式会社ブリヂストン Procédé de production d'un polymère de diène conjugué, polymère de diène conjugué modifié, composition de caoutchouc et pneu
CN108779292A (zh) * 2016-11-01 2018-11-09 株式会社Lg化学 改性共轭二烯类聚合物及其制备方法
WO2019044827A1 (fr) * 2017-09-04 2019-03-07 株式会社ブリヂストン Procédé de production d'un copolymère, copolymère, composition de caoutchouc, et pneumatique
WO2019133633A1 (fr) * 2017-12-30 2019-07-04 Bridgestone Corporation Composition comprenant de multiples polymères à fonctionnalisation terminale
JP7491906B2 (ja) 2019-04-12 2024-05-28 株式会社ブリヂストン ポリイソプレン、ゴム組成物及びタイヤ

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EP3640266A4 (fr) * 2017-06-14 2021-05-12 Bridgestone Corporation Composition de catalyseur, procédé de production de polymère diène conjugué modifié, polymère diène conjugué modifié, composition de caoutchouc et pneumatique
CN111051360B (zh) * 2017-09-04 2022-10-28 株式会社普利司通 聚合催化剂组合物、聚合物制造方法、聚合物、橡胶组合物和轮胎
KR102295642B1 (ko) * 2017-11-21 2021-08-31 주식회사 엘지화학 고무 조성물
CN113166315B (zh) * 2018-12-21 2023-08-01 株式会社Lg化学 改性共轭二烯类聚合物的制备方法
KR102604539B1 (ko) 2019-09-11 2023-11-22 주식회사 엘지화학 변성 공액디엔계 중합체, 이의 제조방법 및 이를 포함하는 고무 조성물
EP3901187A4 (fr) 2019-09-11 2022-03-30 LG Chem, Ltd. Polymère à base de diène conjugué modifié et composition de caoutchouc le comprenant
CN114075307B (zh) * 2020-08-13 2024-03-26 中国石油天然气股份有限公司 稀土催化剂及其制备方法和应用
JP2023063831A (ja) * 2021-10-25 2023-05-10 Ｔｏｙｏ Ｔｉｒｅ株式会社 末端変性ジエン系ポリマー、及びその製造方法
CN116178595B (zh) * 2021-11-26 2024-07-12 中国石油天然气股份有限公司 烯烃聚合用负载茂金属催化剂及其制备方法和应用
CN116178594B (zh) * 2021-11-26 2024-07-16 中国石油天然气股份有限公司 烯烃聚合用原位负载茂金属催化剂及其制备方法和应用

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JPWO2019044827A1 (ja) * 2017-09-04 2020-10-01 株式会社ブリヂストン 共重合体の製造方法、共重合体、ゴム組成物及びタイヤ
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JP7491906B2 (ja) 2019-04-12 2024-05-28 株式会社ブリヂストン ポリイソプレン、ゴム組成物及びタイヤ

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CN106604935B (zh) 2019-02-22
EP3184554B1 (fr) 2019-09-04
RU2671351C2 (ru) 2018-10-30
EP3184554A4 (fr) 2017-08-23
JPWO2016027401A1 (ja) 2017-06-08
RU2017108844A3 (fr) 2018-09-20
EP3184554A1 (fr) 2017-06-28
US20170275400A1 (en) 2017-09-28
CN106604935A (zh) 2017-04-26
JP6645969B2 (ja) 2020-02-14
RU2017108844A (ru) 2018-09-20

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